The reactions of 5,6α-epoxy-3β-hydroxy-5α-cholestane, 5,6β-epoxy-3β-hydroxy-5β-cholestane, and 5,6α-epoxy-3β-methoxy-5α-cholestane with boron trifluoride–ether complex in benzene give largely products of rearrangement via C(5)–O cleavage. These results contrast with the known reactions of the corresponding 3β-acetoxy-epoxides which give high yields of fluorohydrins.
I. G. Guest and B. A. Marples, J. Chem. Soc. C, 1970, 1626 DOI: 10.1039/J39700001626
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